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Sodium Acetate → Ethyl [1-(4-chlorobenzyl)-3-t-butylthio-5-allyloxyindol-2-yl]carboxylate

HRID 1590104
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HRID 1590104 반응식
[C:1]([S:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:25][CH:24]=2)N)=[CH:18][CH:17]=1.CC([O-])=O.[Na+]>C1(C)C=CC=CC=1.CC(O)=O>[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]2[C:23]3[C:24](=[CH:25][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:27][CH:28]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:18][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 517045Sodium AcetateHCID 14919330Ethyl 3-(tert-butylsulfanyl)-2-oxopropanoateHCID 19023706HCID 19023706, 화합물

생성물 1

HCID 21746950Ethyl [1-(4-chlorobenzyl)-3-t-butylthio-5-allyloxyindol-2-yl]carboxylate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140
Toluene
용매

실험 절차

A solution of 18.6 g ethyl 3-t-butylthio-2-oxopropanoate, 26.3 g 1-(4-chlorobenzyl)-1-(4-allyloxyphenyl)hydrazine hydrochloride and 15 g NaOAc in 300 mL toluene and 150 mL HOAc was stirred at room temperature under nitrogen for 16 hours then at 70° C. for 2 hour. The mixture was cooled, poured onto H2O, extracted (3×) EtOAc and the organic layers then washed successively with sat. NaHCO3 and brine. After drying over MgSO4 the solution was filtered, evaporated and the residue chromatographed (silica gel; hexane/EtOAc 4:1) to afford the title compound.

후처리

  1. temperatureThe mixture was cooled
  2. additionpoured onto H2O
  3. extractionextracted (3×) EtOAc
  4. washthe organic layers then washed successively with sat. NaHCO3 and brine
  5. dry with materialAfter drying over MgSO4 the solution
  6. filtrationwas filtered
  7. customevaporated
  8. customthe residue chromatographed (silica gel; hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-1cbcbf23cb1e4bca98ec16b25e53c7a4
출처 데이터셋
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05202321

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